ChiPros^® Chiral Epoxides

Oxiranes are very valuable building blocks which allow derivatization:

• by forming C-X bonds (through reactions with alcohols, ammonia, amines, phenolates etc.)
• or by forming new C–C bonds (through reactions with cyanide, malonates, allyl silyl reagents, metal-organic reagents, e.g. Mg, Zn, Li organyls)

There are several alternative routes towards chiral aryl-substituted epoxides, among them Jacobsen’s asymmetric epoxidation¹ or his hydrolytic kinetic resolution² method, Sharpless’s asymmetric epoxidation^3,4 using catalytic titan(IV)- isopropylate/diethyl tartrate complexes and tert-butylhydroperoxide, complemented by Shi’s reaction^5,6 using peroxomonosulfate with a chiral ketone as catalyst, or among the enzymatic methods, application of epoxide hydrolases, lipases or monooxygenases. The stereoselective reduction of α-chlorinated acetophenones using dehydrogenases, however, affords a very versatile and more cost-efficient access to a wide range of oxiranes, including both enantiomers of styrene oxide as well as very differently substituted phenyl oxiranes (Scheme 1).

Aldrich Chemistry is proud to offer ChiPros^® in small quantities (up to kilograms). A total of 79 products from the ChiPros^® portfolio are available from Aldrich Chemistry, including chiral amines, alcohols, epoxides and carboxylic acids.

ChiPros is a registered trademark of BASF SE